Ruthenium catalyzed oxidation of tertiary nitrogen compounds with molecular oxygen: an easy access to N-oxides under mild conditions

Jain, Suman L.; Sain, Bir

doi:10.1039/b202744p

Cited by 68 publications

(27 citation statements)

References 26 publications

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“…Enhanced charge transfer from Ru 3d to the CO2 2πu antibonding orbital possibly yields chemisorbed CO2δ-species that might act as reaction intermediate to finally produce CO. The activation of CO2 could be promoted by pydc due to the basic pyridyl-N sites in the proximity of the reactive Ru sites (possible pyridyl N-oxide formation [20]). In any way, during synthesis of D1-D3 and formation of reduced Ru +, energy is stored in the system to allow the removal of one O-atom from CO2.…”

mentioning

confidence: 99%

Multifunctional, Defect‐Engineered Metal–Organic Frameworks with Ruthenium Centers: Sorption and Catalytic Properties

et al. 2014

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confidence: 99%

Multifunctional, Defect‐Engineered Metal–Organic Frameworks with Ruthenium Centers: Sorption and Catalytic Properties

et al. 2014

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“…However these reported procedures are suffer from one or more of the drawbacks such as the use of expensive metal catalysts like ruthenium and palladium, addition of bases like potassium carbonate, requirement of sacrificial aldehyde and severe reaction conditions for example high pressure. In continuation to our studies on oxidation using molecular oxygen as primary oxidant [45][46][47]. herein we now report the first successful cobalt (II) Schiff base complexes catalyzed oxidation of secondary alcohols to corresponding ketones in excellent yields with molecular oxygen as the sole oxidant without use of additive (Scheme 1).…”

Section: Introductionmentioning

confidence: 67%

Cobalt (II) Schiff base catalyzed aerobic oxidation of secondary alcohols to ketones

Sharma

Jain

Sain

2004

Journal of Molecular Catalysis A: Chemical

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“…The reaction in H 2 O without oxygen generated no aldehyde product. The oxygen atom was not from ONEt 3 in the reaction because the reaction of 2 a or 2 a' with ONEt 3 [30] in dehydrated CH 2 Cl 2 under nitrogen also gave no aldehyde product. Thus, the oxygen atom in 4 a was confirmed to come from oxygen in air, not from water.…”

Section: Resultsmentioning

confidence: 99%

Cyclization of Aromatic Propargyl Alcohol with a Thiophene Group Yielding Naphthothiophene Aldehyde Induced by a Ruthenium Complex

Tsai

Huang

et al. 2012

Chemistry A European J

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The reactions of [Cp(PPh(3))(2) RuCl] (Cp=cyclopentadienyl) with phenyl propargylic alcohol 1a, with a 3-thiophene group, are explored. The carbene complex 2a, obtained exclusively from this reaction at low temperature, contains the naphthothiophene group, which is formed through a new cyclization process between the thiophene group and the inner carbon of the triple bond. Details of this process have been revealed by conducting the reaction at room temperature, affording the allenylidene complex 3a as a side product. Complex 3a is not converted into 2a, indicating that the cyclization takes place while the triple bond is π coordinated to the metal center. Complex 2a reacts with oxygen in the presence of NEt(3) at room temperature to afford, in high yield, naphthothiophene aldehyde 4a, ONEt(3), OPPh(3), and [Cp(PPh(3))(2)RuCl]. Molecular O(2) is likely activated by coordination to the metal center when one of the phosphane ligands dissociates. Then, NEt(3) promotes the oxygenation process by reacting with the coordinated O(2) to afford ONEt(3) and possibly an unobserved oxo-carbene complex. Coupling of the oxo and carbene ligands then yields 4a and [Cp(PPh(3))(2) RuCl] in CHCl(3). In a solvent system containing MeOH, the oxygenation reaction affords a mixture of 4a and naphthothiophene ester 5a-1. The reactions of [Cp(dppf)RuCl] (dppf=1,1'-bis(diphenylphosphino)ferrocene) with 1a, also afford the carbene complex 2a', 4a, and 5a, which have been characterized by X-ray diffraction analyses. For the phenyl propargylic alcohol 1b, with a 2-thiophene substituent, different naphthothiophene aldehyde and ester compounds are also obtained in high yields through a similar cyclization process followed by oxygenation under mild conditions.

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Ruthenium catalyzed oxidation of tertiary nitrogen compounds with molecular oxygen: an easy access to N-oxides under mild conditions

Abstract: A variety of tertiary nitrogen compounds have been efficiently oxidized to their corresponding N-oxides in excellent yields with molecular oxygen as a sole oxidant and ruthenium trichloride as catalyst.

Cited by 68 publications

References 26 publications

Multifunctional, Defect‐Engineered Metal–Organic Frameworks with Ruthenium Centers: Sorption and Catalytic Properties

Multifunctional, Defect‐Engineered Metal–Organic Frameworks with Ruthenium Centers: Sorption and Catalytic Properties

Cobalt (II) Schiff base catalyzed aerobic oxidation of secondary alcohols to ketones

Cyclization of Aromatic Propargyl Alcohol with a Thiophene Group Yielding Naphthothiophene Aldehyde Induced by a Ruthenium Complex

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